Asking for the Date
Okay – so in our overall “developmental dating” journey, right now you have been coached on how to identify a woman who likes you, and who (hopefully) you like and want to ask out. Now comes the part that some people who have not been single in quite some time dread – the actual act of asking a woman out on a date! How do you do it? How DON’T you do it? Are some ways better than others? The answer is actually very much an individual answer – what works best for some is not necessarily the best for others. Often times the ease of asking a woman out is directly related to how good-looking you are – which never helped me any because I’m very average-looking.

Anytime I planned ahead to ask a woman out, I would almost always be nervous about it. My degree of nervousness was usually a function of how comfortable I was around the woman … how certain I felt my chance of success was. For me, I always did better with women I had known for a while and had a chance to build some sort of rapport with over time. That way I could usually tell if they were interested in me, if they had a current boyfriend, possibly what kind of woman they are, and also what kind of things they liked to do … maybe what kind of food they liked, or what interests they had. It always seemed easier for me to ask a woman out when I knew a lot about her. I would generally ask a woman out on first date to lunch or dinner – in a very easy-going way. In other words, I wouldn’t start out a conversation with a date-shot … rather I would work it into the end of my conversation with her.

"You want to get something to eat after work later this week?”

or maybe

“You want to have lunch with me at <restaurant name> one
day next week?”

The question has to flow within your conversation – so don’t just pop it out, otherwise it might sound weird. Sometimes you might even have to practice it beforehand – but obviously don’t make it sound rehearsed. My advice is that you do not appear overly anxious, and that after you ask – don’t ask a second time. If she is interested in you, you’ll get an answer right away. If she doesn’t answer directly, take that as a “no thank you”, and move on gracefully. Whatever you do, do not pester the woman! That will lump you into the stalker category, and will turn her off (or possibly scare her).

Assuming she agrees to go out with you, the next thing I would typically ask for is her phone number – or some means of contacting her to confirm the date. Again, I would personally do this in a very non-intrusive way, such as

“Can I get your cell number, or should I just call you here
the day before?”

Assuming you are at work, or at her work – it is often less invasive to offer to call her there, if she says it is okay. Some people (myself included) are fairly hesitant to give out our cell numbers until we know someone. Notice that I did not offer up my own cell number in my example dialog … because you just don’t know if a woman is psychotic until you date her at least a few times. In other words, I use my cell phone for work a lot of the time – and the last thing I ever would want is a woman hammering my cell phone with calls during the day … which some women will definitely do. I try to avoid any such possible menaces – so I don’t like to give my cell number out. Expect that some women will feel the same way, and don’t be insulted if she won’t give you her number at first.